Acetonitrile → 2-(N-(4-((4'-chloro-[1,1'-biphenyl]-4-carbonyl)oxy)benzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetic acid

Participants

Reaction Conditions

Reaction Steps

Prepared using General Procedures 16 then 8: To 4-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)methyl)phenyl 4-bromobenzoate INT-10 (50 mg, 0.07 mmol) in a microwave vessel were added Na2CO3 (15 mg, 0.15 mmol), 4-chlorobenzene boronic acid (17 mg, 0.07 mmol), acetonitrile (1 mL) and water (0.1 mL). The suspension was degassed with N2 then treated with PdCl2(dppf) (2.6 mg, 3.64 μmol) and degassed further. The reaction mixture was heated in the microwave at 100° C. for 30 min with stirring. The reaction mixture was diluted with DCM (10 mL) and passed through a phase separator cartridge. The organic layer was isolated and concentrated to 3 mL then TFA (2 mL) was added. After stirring for 2 h at room temperature, the solvent was concentrated and the product was purified by preparative HPLC to provide 17 mg (31%) of 2-(N-(4-((4′-chloro-[1,1′-biphenyl]-4-carbonyl)oxy)benzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetic acid 282. LCMS-ESI (m/z) calculated for C39H30ClF3N2O7: 731; found 732 [M+H]+, tR=8.89 min (Method 9).

Provenance & Evidence